Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: Discovery of YM543

Direkter Zugang zu Azulenen über eine Gold‐katalysierte Dimerisierung von Diarylalkinen

“…Azulen ist ein nichtalternierender Kohlenwasserstoff mit einem großen Dipolmoment [10] und einem kleinen HOMO-LUMO-Abstand. [12] Die elektronische Struktur und die photophysikalischen Eigenschaften machen Azulene hochinteressant fürA nwendungen in organischer Elektronik, [13] biologischer Bildgebung [14] und medizinischer Chemie [15] sowie fürs timuliresponsive Materialien. Daher wäre eine variable Synthese von substituierten Azulenen in wenigen Schritten extrem nützlich.…”

“…Daher wäre eine variable Synthese von substituierten Azulenen in wenigen Schritten extrem nützlich. [12] Die elektronische Struktur und die photophysikalischen Eigenschaften machen Azulene hochinteressant fürA nwendungen in organischer Elektronik, [13] biologischer Bildgebung [14] und medizinischer Chemie [15] sowie fürs timuliresponsive Materialien. [16] Die ersten Synthesen von Azulenen wurden in den 1950er Jahren von Ziegler, Hafner [17] und Nozoe entwickelt.…”

Azulenesulfonium Salts: Accessible, Stable, and Versatile Reagents for Cross‐Coupling

“…[1] Substituted azulenes have been employed in diverse contexts,i ncluding medicinal chemistry (as antiulcer, [2] antidiabetic, [3] anticancer, [4] antiarrhythmic, [5] and anti-erectile-dysfunction [6] agents,a nd as TXA 2 t receptor antagonists [7] ), solar cells, [8] metal-organic frameworks for hydrogen storage, [9] and organic electronics, [10] among others. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling.S pecifically, their application in Suzuki-Miyaura reactions has been demonstrated with ad iverse selection of coupling partners.…”

“…[1] Substituted azulenes have been employed in diverse contexts,i ncluding medicinal chemistry (as antiulcer, [2] antidiabetic, [3] anticancer, [4] antiarrhythmic, [5] and anti-erectile-dysfunction [6] agents,a nd as TXA 2 t receptor antagonists [7] ), solar cells, [8] metal-organic frameworks for hydrogen storage, [9] and organic electronics, [10] among others. [1] Substituted azulenes have been employed in diverse contexts,i ncluding medicinal chemistry (as antiulcer, [2] antidiabetic, [3] anticancer, [4] antiarrhythmic, [5] and anti-erectile-dysfunction [6] agents,a nd as TXA 2 t receptor antagonists [7] ), solar cells, [8] metal-organic frameworks for hydrogen storage, [9] and organic electronics, [10] among others.…”

“…These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides,whichare knownt ob eu nstable and difficult to prepare in pure form.Azulene (1)isanon-alternant aromatic hydrocarbon which has fascinated chemists for many years owing to its blue color and high dipole moment. [1] Substituted azulenes have been employed in diverse contexts,i ncluding medicinal chemistry (as antiulcer, [2] antidiabetic, [3] anticancer, [4] antiarrhythmic, [5] and anti-erectile-dysfunction [6] agents,a nd as TXA 2 t receptor antagonists [7] ), solar cells, [8] metal-organic frameworks for hydrogen storage, [9] and organic electronics, [10] among others. Uses of azulenes in stimuli-responsive systems have also been disclosed, most commonly in halochromic materials, [11] but also in probes for soft metal cations, [12] fluoride, [13] other anions, [14] and biomolecule analytes.…”